A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides

Abhishek Santra, An Xiao, Hai Yu, Wanqing Li, Yanhong Li, Linh Ngo, John B. McArthur, Xi Chen

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

A chemoenzymatic synthon was designed to expand the scope of the chemoenzymatic synthesis of carbohydrates. The synthon was enzymatically converted into carbohydrate analogues, which were readily derivatized chemically to produce the desired targets. The strategy is demonstrated for the synthesis of glycosides containing 7,9-di-N-acetyllegionaminic acid (Leg5,7Ac2), a bacterial nonulosonic acid (NulO) analogue of sialic acid. A versatile library of α2-3/6-linked Leg5,7Ac2-glycosides was built by using chemically synthesized 2,4-diazido-2,4,6-trideoxymannose as a chemoenzymatic synthon for highly efficient one-pot multienzyme (OPME) sialylation followed by downstream chemical conversion of the azido groups into acetamido groups. The syntheses required 10 steps from commercially available d-fucose and had an overall yield of 34–52 %, thus representing a significant improvement over previous methods. Free Leg5,7Ac2 monosaccharide was also synthesized by a sialic acid aldolase-catalyzed reaction.

Original languageEnglish (US)
Pages (from-to)2929-2933
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number11
DOIs
StatePublished - Mar 5 2018

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Glycosides
Mannose
N-acetylneuraminate lyase
Acids
Carbohydrates
Fucose
Monosaccharides
N-Acetylneuraminic Acid

Keywords

  • carbohydrates
  • chemoenzymatic synthesis
  • glycosylation
  • legionaminic acid
  • sialic acid

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides. / Santra, Abhishek; Xiao, An; Yu, Hai; Li, Wanqing; Li, Yanhong; Ngo, Linh; McArthur, John B.; Chen, Xi.

In: Angewandte Chemie - International Edition, Vol. 57, No. 11, 05.03.2018, p. 2929-2933.

Research output: Contribution to journalArticle

Santra, Abhishek ; Xiao, An ; Yu, Hai ; Li, Wanqing ; Li, Yanhong ; Ngo, Linh ; McArthur, John B. ; Chen, Xi. / A Diazido Mannose Analogue as a Chemoenzymatic Synthon for Synthesizing Di-N-acetyllegionaminic Acid-Containing Glycosides. In: Angewandte Chemie - International Edition. 2018 ; Vol. 57, No. 11. pp. 2929-2933.
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